Synthesis of phosphonate analogues of the antibiotic moenomycin A 12:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
2002
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Leipzig, Univ., Diss., 2002 |
| Beschreibung: | 122 Bl. graph. Darst. : 30 cm |
Internformat
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| 100 | 1 | |a Abu Ajaj, Khalid Moh'd |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 |c vorgelegt von Khalid Moh'd Abu Ajaj |
| 264 | 1 | |c 2002 | |
| 300 | |a 122 Bl. |b graph. Darst. : 30 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Leipzig, Univ., Diss., 2002 | ||
| 650 | 0 | 7 | |a Chemische Synthese |0 (DE-588)4133806-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Phosphonate |0 (DE-588)4174406-8 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Weinsäure |0 (DE-588)4189476-5 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Synthon |0 (DE-588)4213140-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Moenomycinanaloga |0 (DE-588)4706181-9 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 689 | 0 | 0 | |a Moenomycinanaloga |0 (DE-588)4706181-9 |D s |
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Datensatz im Suchindex
| _version_ | 1812460519334871040 |
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| adam_text |
CONTENTS
1. INTRODUCTION. 1
1.1 EXISTENCE AND STRUCTURE OF THE MOENOMYCIN ANTIBIOTICS. 1
1.2 STRUCTURAL PROPERTIES OF THE MOENOMYCIN FAMILY. 3
1.3 ANTIMICROBIAL PROPERTIES. 4
1.4 MODE OF ACTION. 4
1.5 STRUCTURE-ACTIVITY RELATIONSHIPS OF THE MOENOMYCINS. 7
1.6 ENZYMATIC DEGRADATION MOENOMYCIN A. 8
1.7 C-GLYCOSIDES. 9
2. PURPOSE OF THE PRESENT WORK. 10
3. PREVIOUS WORK. 11
4. SYNTHETIC DESIGN. 14
4.1 RETROSYNTHETIC ANALYSIS.
.7.
. 14
4.2 PLAN OF SYNTHESIS. 16
5. RESULTS AND DISCUSSION. 20
5.1 SYNTHESIS OF UNIT F-DERIVED GLYCOSYL ACCEPTOR. 20
5.1.1 SYNTHESIS OF ALLY C-GALACTOPYRANOSIDE 34. 20
5.1.2 DOUBLE BOND REARRANGEMENT IN COMPOUND 34. 20
5.1.2.1 PALLADIUM CATALYTIC REACTION OF COMPOUND 34. . 20
5.1.2.2 ENE REACTION. 21
5.1.2.2.1 ATTEMPTED PHOTOOXYGENATION REACTION OF COMPOUND 34. 21
5.1.2.2.2 ENE REACTION OF TRIAZOLINEDIONE WITH COMPOUND 34. 22
5.1.3 PREPARATION OF ALCOHOL 35. 23
5.1.4 PREPARATION OF THE HALIDE DERIVATIVES. 24
5.1.5 HYDROLYSIS OF THE ACETATE GROUP. 25
5.1.6 PREPARATION OF THE SILYL ETHER 63. 26
5.1.7 PREPARATION OF THE ISOPROPYLIDENE DERIVATIVE 53. 26
5.2 SYNTHESIS OF THE DISACCHARIDE BUILDING BLOCK 18. 28
5.2.1 GLYCOSYLATION. 28
5.2.1 1 CHOICE OF THE GLYCOSYL DONOR. 28
5.2.1.2 GLYCOSYLATION MECHANISM. 29
5.2.1.3 SYNTHESIS OF THE GLYCOSYL DONOR. 29
5.2.1.4 DISACCHARIDE FORMATION.
30
BIBLIOGRAFISCHE INFORMATIONEN
HTTP://D-NB.INFO/965277925
5.2.2 CLEAVAGE OF THE SILYL ETHERS IN COMPOUNDS 68 AND 69. 31
5.2.3 SYNTHESIS OF THE URONAMIDE 72. 32
5.2.4 REMOVAL OF THE ISOPROPYLIDENE GROUP FROM 72. 33
5.2.5 CARBAMOYLATION. 34
5.2.5.1 TRIAL BASED ON TAI. 35
5.2.5.2 TRIAL BASED ON THE PHENYL CARBONATE 75. 36
5.2.5.3 AMINOLYSIS OF THE CYCLIC CARBONATE 76. 37
5.2.6 FORMATION OF THE ACETAMIDE. 38
5.2.6.1 REMOVAL OF THE TRICHLOROACETYL GROUP IN COMPOUND 76. 39
5.2.6.1.1 HYDROLYSIS WITH LIOH. 39
5.2.6.1.2 REDUCTION WITH NABH
4
. 40
5.2.6.2 REDUCTION OF THE N-TRICHLOROACETYL GROUP IN COMPOUND 74 WITH
NABH
4
42
5.2.7 PHOSPHONATE FORMATION.
:T. 44
5.2.8 CONCLUSION AND SUGGESTIONS FOR FURTHER WORK. 44
5.3 SYNTHESIS OF THE TRISACCHARIDE BUILDING BLOCK 19. 45
5.3.1 TRIALS TO PREPARE 87 BASED ON OXAZOLINE 42. 45
5.3.2 SYNTHESIS BASED ON THE TRICHLOROACETAMIDATE DONOR 88. 46
5.3.2.1 SYNTHESIS OF THE DONOR 88. 46
5.3.2.2 SYNTHESIS OF THE GLYCOSYL ACCEPTOR 92. 47
5.3.2.3 GLYCOSYLATION TRIAL BASED ON ACCEPTOR 92. 48
5.3.2.4 SYNTHESIS OF THE GLYCOSYL ACCEPTOR 95. 49
5.3.2.5 GLYCOSYLATION BASED ON ACCEPTOR 95. 49
5.3.3 CLEAVAGE OF THE TBDMS GROUP IN 96. ^
5.3.4 SYNTHESIS OF THE URONAMIDE 93. ^
5.3.5 SYNTHESIS TRIAL OF 103. ^ *
5.3.6 CONCLUSION AND SUGGESTIONS FOR FURTHER WORK.
$2
6. SUMMARY. ^
7. EXPERIMENTAL PART. ^
7.1 DEVICES, METHODS AND MATERIALS . ^
CQ
7.1.1 DEVICES USED.
7.1.2 METHODS USED.
(O
7.1.3 CHEMICALS AND SOLVENTS USED.
7.2 PREPARATION OF THE GLYCOSYL ACCEPTOR 53. 63
7.2.1 PREPARATION OF 34. 63
7.2.2 DOUBLE BOND REARRANGEMENT REACTION OF 34. 63
7.2.2.1 PHOTOOXYGENATION REACTION OF 34. 63
7.2.2.1.1 USING METHYLENE BLUE. 63
7.2.2.1.2 USING ROSE BENGAL. 64
1222
PALLADIUM CATALYTIC REACTION OF 34. 64
1223
ENE REACTION OF COMPOUND 34 WITH PTAD. 65
7.2.3 PREPARATION OF ALCOHOL 35. 66
7.2.4 PREPARATION OF METHANESULPHONATE 60. 69
7.2.5 PREPARATION OF THE HALIDE DERIVATIVES 59 AND 61. 70
7.2.5.1 PREPARATION OF COMPOUND 61. 70
12.52
PREPARATION OF COMPOUND 59. 71
7.2.6 HYDROLYSIS OF THE ACETATE GROUP IN 61. 72
7.2.7 PREPARATION OF THE SILYL ETHER 63. 73
7.2.8 PREPARATION OF THE ACCEPTOR 53. 74
7.3 DISACCHARIDE SYNTHESIS. 76
7.3.1 FORMATION OF DISACCHARIDE 68. 76
7.3.2 CLEAVAGE OF THE SILYL ETHERS IN 68 AND 69. 715
7.3.2.1 REACTION OF COMPOUND 69 WITH DOWEX RESIN. 715
7.3.2.2 REACTION OF COMPOUND 68 WITH TBAF. 79
7.3.3 PREPARATION OF THE URONAMIDE 72.
8^
82
7.3.4 REMOVAL OF THE ISOPROPYLIDENE GROUP FROM 72.
81
7.3.5 PREPARATION OF CYCLIC CARBONATE 76.
O
7.3.6 SYNTHESIS OF URETHANE 74.
7.3.6.1 TRIAL BASED ON TAI.
85
7.3.6.2 TRIAL BASED ON PHENYL CARBONATE.
85
7.3.6.3 RING OPENING OF 76 WITH AMMONIA.
88
7.3.7 DEHALOGENATION OF THE TRICHLOROACETAMIDO GROUP.
7.3.7.1 TRIALS BASED ON 76.
88
7.3.7.1.1 HYDROLYSIS WITH LIOH.
88
7.3.7.1.2 REDUCTION WITH NABFLJ.
8^
91
7.3.7.2 REDUCTION OF 74 WITH NABFLJ.
7.3.7.3 REDUCTION OF 80 WITH NABHACN. 93
7.3.8 SYNTHESIS OF PHOSPHONATE 85. 93
7.4 TRISACCHARIDE SYNTHESIS. 95
7.4.1 TRIALS TO PREPARE TRISACCHARIDE 87 BASED ON OXAZOLINE 42. 95
7.4.1.1 SYNTHESIS OF THE OXAZOLINE DONOR 42. 95
7.4.1.2 TRIALS BASED ON THE OXAZOLINE 42. 95
7.4.2 PREPARATION OF THE ACCEPTOR 92. 96
7.4.2.1 ACETYLATION OF COMPOUND 53. 96
7.4.2.2 CLEAVAGE OF THE SILYL GROUP IN 89. 97
7.4.2.3 PREPARATION OF THE URONAMIDE 91. 98
7.4.2.4 PREPARATION OF THE ACCEPTOR 92. 99
7.4.3 TRIALS TO PREPARE TRISACCHARIDE 93 BASED ON ACCEPTOR 92. 100
7.4.4 SYNTHESIS OF THE ACCEPTOR 95.
7.
101
7.4.4.1 PREPARATION OF THE SILYL ETHER 94. 101
7.4.4.2 PREPARATION OF THE ACCEPTOR 95. 102
7.4.5 PREPARATION OF TRISACCHARIDE 96 BASED ON ACCEPTOR 95. 103
7.4.6 CLEAVAGE OF THE TBDMS ETHER IN 96. 105
7.4.7 SYNTHESIS OF THE URONAMIDE 93. 106
7.4.8 SYNTHESIS TRIAL OF 103. 108
7.4.9 SYNTHESIS TRIAL OF 100. 110
8. ABBREVIATIONS. ^
9. REFERENCES. ^ |
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| indexdate | 2024-10-09T18:04:06Z |
| institution | BVB |
| language | English |
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| physical | 122 Bl. graph. Darst. : 30 cm |
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| spelling | Abu Ajaj, Khalid Moh'd Verfasser aut Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 vorgelegt von Khalid Moh'd Abu Ajaj 2002 122 Bl. graph. Darst. : 30 cm txt rdacontent n rdamedia nc rdacarrier Leipzig, Univ., Diss., 2002 Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Phosphonate (DE-588)4174406-8 gnd rswk-swf Weinsäure (DE-588)4189476-5 gnd rswk-swf Synthon (DE-588)4213140-6 gnd rswk-swf Moenomycinanaloga (DE-588)4706181-9 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Moenomycinanaloga (DE-588)4706181-9 s Phosphonate (DE-588)4174406-8 s Chemische Synthese (DE-588)4133806-6 s Weinsäure (DE-588)4189476-5 s Synthon (DE-588)4213140-6 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010129972&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Abu Ajaj, Khalid Moh'd Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 Chemische Synthese (DE-588)4133806-6 gnd Phosphonate (DE-588)4174406-8 gnd Weinsäure (DE-588)4189476-5 gnd Synthon (DE-588)4213140-6 gnd Moenomycinanaloga (DE-588)4706181-9 gnd |
| subject_GND | (DE-588)4133806-6 (DE-588)4174406-8 (DE-588)4189476-5 (DE-588)4213140-6 (DE-588)4706181-9 (DE-588)4113937-9 |
| title | Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 |
| title_auth | Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 |
| title_exact_search | Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 |
| title_full | Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 vorgelegt von Khalid Moh'd Abu Ajaj |
| title_fullStr | Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 vorgelegt von Khalid Moh'd Abu Ajaj |
| title_full_unstemmed | Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 vorgelegt von Khalid Moh'd Abu Ajaj |
| title_short | Synthesis of phosphonate analogues of the antibiotic moenomycin A 12 |
| title_sort | synthesis of phosphonate analogues of the antibiotic moenomycin a 12 |
| topic | Chemische Synthese (DE-588)4133806-6 gnd Phosphonate (DE-588)4174406-8 gnd Weinsäure (DE-588)4189476-5 gnd Synthon (DE-588)4213140-6 gnd Moenomycinanaloga (DE-588)4706181-9 gnd |
| topic_facet | Chemische Synthese Phosphonate Weinsäure Synthon Moenomycinanaloga Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010129972&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT abuajajkhalidmohd synthesisofphosphonateanaloguesoftheantibioticmoenomycina12 |